Clyde, for his part, started out on his life of crime at a tender age. His first arrest took place before he had turned 18 for failing to bring back a rental car. More petty crime followed for him, sometimes in the company of his elder brother Buck – until Clyde was sent to the Eastham Prison Farm in 1930.
While incarcerated, Clyde beat to death another prisoner with a lead pipe, apparently after the man had sexually assaulted him. However, another prisoner, serving life, took the rap for the killing. Clyde also later convinced an inmate to chop off a pair of his toes so that he could avoid the arduous prison farm work. He was therefore left with a permanent limp. Yet unbeknownst to Clyde, he was only six days away from an early prison release thanks to a petition from his mother.
Clyde was let out of Eastham in February 1932, but doing time seems to have taken its toll. A fellow prisoner remembered that he “change[d] from a schoolboy to a rattlesnake” while serving his sentence there. And one of Clyde’s sisters would later say, “Something awful sure must have happened to him in prison because he wasn’t the same person when he got out.” It’s also been reported that Barrow was subsequently obsessed with exacting revenge on Eastham.